


Ride 'Im, Cowboy

by orphan_account



Series: DeanBenny Daddykink [5]
Category: Supernatural
Genre: Adult Man Roleplaying Underage Boy, Alternate Universe - Canon Divergence, Cowboy Kink, Daddy Kink, Dress Up, M/M, Underage Roleplay
Language: English
Status: Completed
Published: 2013-09-05
Updated: 2013-09-05
Packaged: 2017-12-25 16:23:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,638
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/955245
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Dean plays dress-up for Benny.</p>
            </blockquote>





	Ride 'Im, Cowboy

Benny loved it when it had been a while since Dean was on a hunt. Because that meant that Dean got even more creative with what to do in bed. 

And Benny had been pretty excited when Dean proposed that they put some of his disguises that he had held onto, even if they were only for one-time situations on the job, to good use. 

Benny did have a thing for plenty of Dean's outfits. Plaid was fine, yeah, but damn if he didn't look fine in that FBI suit. But what had really caught Benny's attention had been the cowboy outfit. 

"What'd you wear this for?" Benny asked, picking up the cowboy hat from the shelf in the closet. 

Dean smirked as he looked over to see what Benny was talking about. 

" _That_ was for when Sam and I went back in time to meet Samuel Colt to find phoenix ashes." 

"You had to go back in time for that? How'd you manage?"

"Cas."

"Ah."

Benny put the cowboy hat on top of Dean's head. 

"You look cute in it," Benny remarked, smirking back at him. 

"I know. The clothes were too clean for the time period; Sam and I both came off as really gay."

"You are really gay, darlin'."

Dean laughed, then closed the gap between them. 

"Well, of course I'm really gay for Daddy. Daddy's cock is so big and thick and feels so good thrusting in and outta me, and his come is so tasty." 

Benny's eyebrows flew up, and he could feel the growing erection coming on. 

"I'm glad my baby boy thinks so," Benny replied, bringing a hand up to caress the side of Dean's face. 

At the time, Dean had taken off the cowboy hat, and he blew Benny right there in the closet, falling to his knees and deep-throating him like a porn star, Benny running his fingers through Dean's hair and telling him what a good little boy he was. But afterwards, Dean brought up the topic of the cowboy outfit again. 

"I mean, if you want me to, I can wear it. Then we can play cowboy and you can show me how to really ride." Complete with lick of his lips and batting of his eyelashes which he basically perfected from his naïve little boy act. 

Dean Winchester was going to be the death of him. 

"Hell yes I want you to wear it," Benny replied, and Dean grinned at him. 

So here they were, on a Saturday and having absolutely no plans to leave the house. All house calls were going to go to the answering machine, cell phone calls were going to voice mail, and they were going to stay in the bedroom unless one of them wanted to fuck on the kitchen table or the couch. (And to eat.) Dean was putting the finishing touches on his costume, taking care to make sure all his buttons were buttoned up properly, even though they were just going to disrobe him again. When he put the cowboy hat on, he looked himself over in the mirror for a few seconds, then smiled and winked at himself before taking a deep breath and getting into character. 

Once he had done so, Dean turned around and gave Benny that look of pure adoration mixed with naivety that he wore so well. 

"How do I look, Daddy?" 

Benny walked over to him, giving him a once-over. He smiled at him. 

"You look gorgeous, sweetheart." 

Dean smiled back, and he swayed back and forth for a moment or two. 

"Daddy ready to play?" 

"Mm-hm. You might have to fill me in a little, darlin', it's been a while since I was your age."

Dean's smile widened, and he took hold of Benny's arm in a way that imitated an excited child's. 

"You lie on your back on the bed, and I straddle you, and then I ride you." 

"Just like that?" Benny said, smirking and raising an eyebrow. 

Dean nodded; they both knew full well Dean was still going to play up the naïve aspect of his character, so clearly it wasn't going to be as simple as that, but that was part of the fun. 

Benny did as instructed, moving onto the bed and lying down on it. Dean hopped up onto the bed and straddled Benny, his thighs on either side of his waist. For the next few minutes, Dean grinded against Benny's crotch, providing the friction and pressure that Benny would need to help awaken his cock. Benny moaned with each brush of fabric against fabric, crotch against ass and perineum, and his pupils dilated as he watched Dean's erection grow through his pants. Dean huffed and groaned as he bounced up and down and back and forth on Benny, his own pupils growing wider. 

"Are you having fun, Daddy?" Dean asked, rocking back and forth. 

"Mmmm, yeah, darlin'. I just think I've thought of a way to make this even more fun." 

"Oh?" Dean said, slowing his hips. "What is it, Daddy?" 

Benny grinned at him in a rather predatory way. 

"Think my baby boy can ride me while my hard cock is up your ass?" 

Dean shivered with anticipation, and Benny could feel the trembling of his body against him. It made his grin widen. 

"Uh huh - yes, Daddy, I think I can do that." 

Benny reached up and kissed Dean as they slid Dean off of his crotch, but just long enough to get Dean out of his pants and underwear enough to actually reach his cock and hole, then undo Benny's belt and zipper, push those down to access Benny's cock and pull it out. Dean licked his lips as it came into view. 

"Daddy's cock wants to come out to play~" Dean said, giving Benny _that look_ that made him want to pin Dean down and fuck the daylights out of him. 

"You bet it does," Benny said, his accent becoming thicker to match his growing lust. 

Dean started to crawl back onto Benny, and Benny lay back down, watching Dean, watching as Dean pushed himself down on Benny's cock, watching Dean's mouth fall open as the head of his cock became surrounded by his warm flesh. Benny moaned as his erection became sheathed inside Dean's body. Dean panted and moaned and whimpered, letting himself get used to the feeling of the intrusion once more before he started to move again, slowly at first, then gathering momentum as the thrusts would hit his prostate and reach far deep inside of him, the head of Benny's cock hitting spots inside that Dean would be embarrassed to admit that he liked the feeling of it. 

Benny placed his hands on Dean's hips to help guide him, grunting in tandem with each sound of flesh slapping against flesh, the sounds becoming more frequent the faster Dean would ride him. 

"Oh~! Oh _Daddy_!" Dean cried out, having to brace himself by putting his hands on Benny's shoulders. Benny took a bit more control, moving his hips into Dean's thrusts more and bettering his grip on Dean's hips. "Daddy, Daddy, Daddy, _Daddy,_ it feels so good, so good inside me, Daddy, so thick and warm and _uuuuuhhh-aaah_ \- so deep inside me, Daddy, how do you fit Daddy, how - _oh Daddy yes, hard like that, yes_ \- you're so good to me, Daddy!" 

Benny focused on thrusting upward, snapping into Dean's hips. 

"Such a good boy, Dean, a very, very good boy. So tight for your old man, aren't ya? You take it so well, darlin', such a good baby boy you are."

Dean _mewled_ and positively glowed from the praise. Benny managed to smirk despite everything. 

"My little boy fucks me so well, don't you, baby?" 

Dean nodded, panting hard, trying to catch his breath. 

"Make all the other daddies jealous, don't you?"

Dean managed to blush, but he couldn't drum up a response because Benny snapped his hips up and made him cry out even more in pleasure. 

When Dean managed to talk again, he had to gasp it out. 

"Daddy's so good to me, best Daddy ever. Anyone would love to be with Daddy."

Benny changed their pace, going from snapping wildly up into Dean to holding Dean up against his hips and situating himself into a sitting position instead, Dean cooperating and allowing Benny to maneuver him as needed. 

"Well, you've got your old man all to yourself," Benny said, using his hands to monitor the pace for Dean to continue to grind against him. Dean complied, and he moaned loudly as Benny took his cock into his hand and started to jack Dean off. 

"Daddy - !" 

Dean gasped loudly as Benny came inside of him, and Dean spurted his come over his and Benny's stomachs and chests soon after. Dean bit his lip and mewled a little as he felt Benny's come leak out of his ass around Benny's cock. 

They allowed themselves a while to catch their breath. Then - 

"What about when we invite Cas over?" 

Benny raised an eyebrow at Dean. 

"You honestly think Cas would want to touch me in the slightest when we have that threesome?"

Dean managed to blush, the redness coming over both his cheeks. 

"It's totally you we're both going to be focusing on. And knowing us, we'll probably start arguing on what's gonna make you beg louder."

Dean laughed. 

"Well, maybe you should decide beforehand what we'll be doing." 

"Just me?" 

Dean gave him a cheeky grin. 

"Yeah. 'Cause I can't decide if I want you two to double penetrate me or if I want to be fucked from both ends." 

Benny growled, and Dean's grin widened. 

"Baby, you're gonna be the death of me."

"It'll be a fun one." 

It was Benny's turn to laugh.


End file.
